Sodium Hydroxide → 2-(3,4-Dichloro-phenyl)-oxirane

HRID 576100

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HRID 576100 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=[O:4].[BH4-].[Na+].[OH-].[Na+]>CO>[Cl:12][C:7]1[CH:6]=[C:5]([CH:3]2[CH2:2][O:4]2)[CH:10]=[CH:9][C:8]=1[Cl:11]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 4311764Sodium borohydride

생성물 1

HCID 135217142-(3,4-Dichloro-phenyl)-oxirane수율 50%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of 2-bromo-1-(3,4-dichlorophenyl)ethanone (5.1 g, 18.96 mmol) in methanol (50 mL) at 0° C. was added sodium borohydride (2.1 g, 56.98 mmol). The reaction mixture was stirred at 0° C. for 1 hour. The pH was adjusted to 12 using 2 M sodium hydroxide solution, the solvent was then removed under reduced pressure and the residue was dissolved in dichloromethane. The resultant solution was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give 2-(3,4-dichlorophenyl)oxirane (1.79 g, 50% crude). The crude product was used in the next step without further purification: 1H NMR (CDCl3, 500 MHz) δ 7.41 (d, J=8.5 Hz, 1H), 7.36 (d, J=2.0 Hz, 1H), 7.12 (dd, J=8.5, 2.0 Hz, 1H), 3.81 (dd, J=4.0, 2.5 Hz, 1H), 3.14 (dd, J=5.5, 4.0 Hz, 1H), 2.73 (dd, J=5.5, 2.5 Hz, 1H); ESI MS m/z 189 [M]+.

후처리

  1. customthe solvent was then removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resultant solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-abc6a233c7964b5585f5a1c521fdf845
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034899B2

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